35458-39-0Relevant articles and documents
Dehydrogenative coupling to enable the enantioselective total synthesis of (-)-simaomicin α
Wang, Yizhong,Wang, Chao,Butler, John R.,Ready, Joseph M.
, p. 10796 - 10799 (2013)
The anticancer natural product simaomicin α has been synthesized. Asymmetric synthesis allowed the assignment of absolute stereochemistry. The enantiomer of the naturally occurring substance shows potent cytotoxicity towards Gram-positive bacteria and human cancer cells. Bn=benzyl, BOM=benzyloxymethyl. Copyright
Process Development and Scale-up of Fully Synthetic Tetracycline TP-2758: A Potent Antibacterial Agent with Excellent Oral Bioavailability
Zhang, Wu-Yan,Sun, Cuixiang,Hunt, Diana,He, Minsheng,Deng, Yonghong,Zhu, Zhijian,Chen, Chi-Li,Katz, Christopher E.,Niu, John,Hogan, Philip C.,Xiao, Xiao-Yi,Dunwoody, Nicholas,Ronn, Magnus
, p. 284 - 296 (2016/03/04)
Process research and development of the fully synthetic broad spectrum tetracycline TP-2758, with a chiral pyrrolidine side chain at the C-8 position, is described. The process utilizes two key intermediates, 7 and 10, in a convergent approach that allows for manufacturing of sufficient quantities of API to supply preclinical and early clinical development. The pyrrolidine moiety was introduced into the left-hand piece (LHP) 10 with high enantioselectivity using Ellman's sulfinamide chemistry, and the absolute configuration was confirmed by X-ray crystal structure analysis.
Storable arylpalladium(II) reagents for alkene labeling in aqueous media
Simmons, Rebecca L.,Yu, Robert T.,Myers, Andrew G.
, p. 15870 - 15873 (2011/11/13)
We show that arylpalladium(II) reagents linked to biotin and indocyanine dye residues can be prepared by decarboxylative palladation of appropriately substituted electron-rich benzoic acid derivatives. When prepared under the conditions described, these organometallic intermediates are tolerant of air and water, can be stored for several months in solution in dimethyl sulfoxide, and permit biotin- and indocyanine dye-labeling of functionally complex olefinic substrates in water by Heck-type coupling reactions.